The mechanism of catalytic enantioselective fluorination: Computational and experimental studies

Piana, StefanoDevillers, IngridTogni, AntonioRothlisberger, Ursula2006-02-272006-02-272006-02-27200210.1002/1521-3773(20020315)41:6<979::AID-ANIE979>3.0.CO;2-Ehttps://infoscience.epfl.ch/handle/20.500.14299/226173A parallel orientation between the coordinated substrate enolate and a face-on naphthyl group of the TAD-DOL ligand control the stereochem. outcome of the Ti-catalyzed asym. fluorination of 1,3-dicarbonyl compds. with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanetriethylenediamine (F-TEDA). D. functional theory based quantum-mech. mol. mech. calcns. also disclose the fluorine-transfer step as occurring by a single-electron transfer. [on SciFinder (R)]The mechanism of catalytic enantioselective fluorination: Computational and experimental studiestext::journal::journal article::research article